CARBOHYDRATES

 Most abundant organic compounds in the plant  FISCHER PROJECTION FORMULAS

word  Glyceraldehyde – contains a stereocenter and
 Act as storehouse of chemical energy therefore exists as a pair of enantiomers

 Components of supporting structures in plants  Enantiomer – is one of two

o Crustacean shells i. D- and L- Monosaccharides

o Connective tissues in animals  D-Monosaccharides

a. Has the -OH group on its
o Essential components of nucleic acids
penultimate carbon to the right
 Means “HYDRATE OF CARBON”
 L-Monosaccharides
 Derives from the formula “Cn(H2O)m”
a. Jas the -OH group on its
o Glucose: C6H12O6
penultimate carbon to the left
 Most are polyhydroxyaldehydes, polyhydroxy
 Physical Properties
ketones, or compounds that yield them after
i. Are colorless, crystalline solids
hydrolysis
ii. Are very soluble in water
 Saccharides – simpler members of CHO family
 Because hydrogen bonding is
(Latin: SACHHARUM – SUGAR)
possible between their polar-OH
o Monosaccharides, disaccharides,
groups and water
oligosaccharides, and polysaccharides
 Slightly soluble in ethanol
 Insoluble in nonpolar solvents such
1. Monosaccharides
as diethyl ether, dichloromethane,
 C6H12O6
and benzene
 With one off the carbon being the carbonyl
 Cyclic Structure
group of either an aldehyde or ketone
i. Haworth Projection (at least 5 carbons)
 Have 3 to 9 carbon atoms
 A way to view furanose and
 -ose indicates that a molecule is a
pyranose forms of monosaccharides
carbohydrate
 The rings are drawn flat and viewed
 Tri-, tetr-, pent-, indicate the number of
through its edge with anomeric
carbon atoms in the chain
carbon on the right and the oxygen
i. Aldoses
on the rear
 Monosaccharides containing an
 A 5- or 6- membered cyclic carbon
aldehyde group
 B means that the -OH on the
ii. Ketoses
anomeric carbon lies on the same
 Monosaccharides containing a
side of the ring as the termina
ketone
CH2OH
iii. 2 Trioses
 -pyran- a 6-membered hemiacetal
 Aldotriose Glyceraldehyde
ring
 Ketotriose Dihydroxyacetone
 -furan- a 5-membered hemiacetal
ring
  Pyranose and Furanose  D-Mannosamine
a. Are used because 2. Disaccharides
monosaccharides 5- and 6-  Contain 2 monosaccharides unites joined by
membered rings correspond to glycosidic bond
the heterocyclic compounds 3. Oligosaccharides
pyran and furan  To describe any of the carbohydrates
 Reactions of Monosaccharides
i. Oxidation to produce acidic sugars
 Oxidation of the aldehyde end of
glucose produces GLUCONATE
ii. Oxidation to Uronic Acids
 Enzyme-catalyzed oxidation of the
primary alcohol at carbon 6 of a
hexose yields a uronic acid
iii. Reduction to Produce Sugar Alcohols
 Carbonyl group is reduced to a
hydroxyl group using hydrogen as
the reducing agent (sugar alcohol)
 Drop -ose and change to -itol
 Xylitol – used as a sweetening agent
in “sugarless” products
 Formation of Glycosides (Acetals)
i. Acetals – yields when hemiacetal
(derived from aldehyde) is treated with
one molecule of alcohol
ii. Glycoside
 A carbohydrate in which the -OH
group on its anomeric carbon is
replaced by an -OR group
iii. Glycosidic Bond
 The bond from the
 Phosphate Esters Formation
i. Important in the metabolism pf
monosaccharides
ii. Conversion of glucose to glucose-6-
phosphate
 Amino Sugar Formation
i. A monosaccharide in which an -OH
group is replaced by an -NH2 group
 D-Glucosamine